EP0131258B1 - Urées N-alkoxy- et N-alkylsulfonylaminosulfonyliques et pyrimido- ou triazino-thiatriazine-oxides comme intermédiaires - Google Patents

Urées N-alkoxy- et N-alkylsulfonylaminosulfonyliques et pyrimido- ou triazino-thiatriazine-oxides comme intermédiaires Download PDF

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Publication number
EP0131258B1
EP0131258B1 EP84107833A EP84107833A EP0131258B1 EP 0131258 B1 EP0131258 B1 EP 0131258B1 EP 84107833 A EP84107833 A EP 84107833A EP 84107833 A EP84107833 A EP 84107833A EP 0131258 B1 EP0131258 B1 EP 0131258B1
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Prior art keywords
formula
compounds
alkoxy
alkyl
denotes
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EP84107833A
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German (de)
English (en)
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EP0131258A2 (fr
EP0131258A3 (en
Inventor
Lothar Dr. Willms
Hilmar Dr. Mildenberger
Klaus Dr. Bauer
Helmut Dr. Bürstell
Hermann Dr. Bieringer
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Bayer CropScience AG
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Hoechst AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • heterocyclically substituted phenylsulfonylureas have herbicidal or plant growth-regulating properties s. e.g. B. NL-A 121 788, DE-A 27 15 786, EP-A 1485, DE-A 3243 533.
  • DE-A 3 243 533 describes those ureas which carry a substituted amino radical on the sulfonyl group.
  • these have disadvantages in use, such as high persistence or insufficient selectivity.
  • heterocyclically substituted N-alkoxy- and N-alkylsulfonylaminosulfonylureas which contain a pyrimidine or triazine ring as a heterocyclic component are particularly suitable as herbicides and plant growth regulators.
  • Halogen preferably means fluorine, chlorine or bromine.
  • the invention also relates to new (pyrimido) triazino-thiatriazine oxides of the formula (II) which, as stated below, can act as intermediates for the preparation of the compounds of the formula (I) according to the invention.
  • the new compounds of the general formula I can be synthesized from starting materials known per se or from starting materials prepared by known processes.
  • the reaction of the compounds (111) and (IV) is preferably carried out in inert aprotic solvents such as aliphatic or aromatic hydrocarbons, in particular n-hexane, toluene or xylene, acetonitrile, dichloromethane, chloroform, nitromethane, tetrahydrofuran, or dioxane at temperatures between - 78 ° C and the boiling point of the solvent, preferably in the presence of an acid acceptor such as a tertiary organic amine, especially pyridine or triethylamine or an inorganic base such as an alkali carbonate.
  • X oxygen
  • the compound (III) can be used in excess in order to act as an auxiliary base at the same time.
  • the same solvents are preferably used as in a) and the process is carried out at temperatures between ⁇ 78 ° C. and the boiling point of the solvent. If appropriate, the reaction is carried out with the addition of one or more equivalents of basic compounds, such as tertiary organic amines, in particular triethylamine, ethyldiisopropylamine, pyridine or on organic bases such as potassium carbonate.
  • basic compounds such as tertiary organic amines, in particular triethylamine, ethyldiisopropylamine, pyridine or on organic bases such as potassium carbonate.
  • acylation of amino heterocycles of the formula VI with sulfonyl isocyanates of the formula V is preferably carried out in the same solvents mentioned under a) at temperatures between ⁇ 20 ° C. and the boiling point of the solvent.
  • inert solvents such as.
  • Conventional agents such as dimethyl sulfate; Methyl iodide or ethyl bromide used.
  • salts of the formula I in which R 2 or R 3 is hydrogen can form salts in which H is replaced by a suitable cation.
  • These salts are generally metal, especially alkali or alkaline earth metal salts, optionally alkylated ammonium or organic amine salts and are preferably in inert solvents such as. B. water, methanol or acetone at temperatures of 20-100 ° C.
  • Suitable bases for the preparation of the salts according to the invention are e.g. B. alkali carbonates, ammonia or ethanolamine.
  • the starting materials of the formula (II) required for the preparation of the compounds of the general formula (I) according to the invention are new and can be obtained in particular by addition of chloro- or fluorosulfonyl isocyanate to aminoheterocycles of the above-mentioned formula (VI) in the presence of bases such as tertiary organic amines Triethylamine or ethyldiisopropylamine.
  • bases such as tertiary organic amines Triethylamine or ethyldiisopropylamine.
  • the compounds of the formula II and their preparation process are therefore also an object of the invention. This process is preferably carried out in inert organic solvents such as dichloromethane, acetonitrile, tetrahydrofuran at temperatures between -78 ° C and + 40 ° C.
  • R 5 , R6 (C 1 -C 4 ) alkylamino or (C 1 -C 4 ) dialkylamino
  • this method of preparation of the compounds of the formula II is less suitable because of low yields.
  • These regioisomer mixtures can be separated by customary methods such as recrystallization, chromatography, etc.
  • the starting materials of the formula III are known or can be prepared by processes which are known in principle.
  • the corresponding hydroxylamines of formula (III) (X O) z. B. by alkaline hydrolysis of alkylalkoxycarbamic esters s. Appl. 75, 851 (1963).
  • EP-A-39 239, for Z A lkoxy s.
  • EP-A-61 661, for Z phenoxy see. GB-A-2015 503.
  • the sulfonyl isocyanates of the formula (V) are prepared by reacting chlorosulfonyl isocyanate with secondary aliphatic sulfonamides (DE-A-2 257 240).
  • the starting materials of formula IV are known or can be prepared by processes known in principle, e.g. B. by cyclizing corresponding guanidine derivatives with appropriately substituted 1,3-diketones, see, for. B. "The Chemistry of Heterocyclic Compounds", Vol. XVI (1962) and Supplement I (1970) or by derivatization of cyanuric chloride, cf. B. "The Chemistry of Heterocyclic Compounds", L. Rapoport: "s-Triazines and Derivatives” (195 9 ).
  • the heterocyclic sulfonylurea derivatives according to the invention have an excellent herbicidal action and very good selectivity in important large crops. They are therefore suitable for the selective control of dicotyledonous and grassy annual and perennial weeds, in particular in agriculturally important crops such as, for. B. wheat, barley, rye, rice, corn, sugar beet and soy. It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence spraying. If the compounds according to the invention are applied to the surface of the earth in a pre-sowing or pre-emergence process prior to the germination of the weed plants, the emergence of the seedlings is not prevented.
  • the weeds grow to the cotyledon stage, but then stop growing and eventually die completely after 3-5 weeks.
  • the active ingredients are applied to the green parts of the plant in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the crop plants harmful weed competition is eliminated very early and sustainably.
  • the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. B. by triggering desiccation and stunted growth. They are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage. Particularly noteworthy is the growth regulatory activity of the compounds as growth inhibitors in cereals, maize, soybeans, cotton, lawn and their ability to increase the content of desired ingredients such as carbohydrates and protein in crops. Finally, the compounds show a very good improvement in fruit abscess, especially in the case of citrus fruits, or a reduction in the holding power.
  • the invention therefore also relates to herbicidal and growth-regulating agents which are characterized by a content of a compound of the formula I in combination with customary formulation auxiliaries and inert substances and their use in the agricultural field.
  • the agents according to the invention generally contain the active ingredients of the formula I in an amount of 2-95% by weight. They can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the usual preparations.
  • the wettable powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, in addition to a diluent or inert substance, are also wetting agents, for B. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenyl sulfonates and dispersants, e.g. B. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleylmethyl tauric acid sodium.
  • B. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenyl sulfonates and dispersants e.g. B. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • emulsifiers e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons
  • emulsifiers e.g. B. butanol, cyclohexanone, dimethylformamide
  • Alkylarylsulfonic acid calcium salts such as Ca-dodecyl-benzosulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol propylene oxide-ethylene oxide condensation products, alkyl polyether acid or sorbitan ethoxylate, sorbitan ethoxylate, sorbitan ethoxylate, sorbitan ethoxylate, sorbitan ethoxylate, sorbitan ethoxylate.
  • Dusts are obtained by grinding the active ingredient with finely divided, solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
  • finely divided, solid substances e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives e.g. B. polyvinyl alcohol, sodium polyacrylic acid or mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be produced in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • adhesives e.g. B. polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Suitable active ingredients can also be produced in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • the concentrations of the active compounds in the commercial formulations can vary.
  • the active ingredient concentration varies e.g. B. between about 10% and 80%, the rest consists of the formulation additives specified above. In the case of emulsifiable concentrates, the active substance concentration can likewise be approximately 10% to 80%. Dust-like formulations contain about 2-20%. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.
  • the commercially available concentrates are optionally diluted in the customary manner, for. B. with wettable powders and emulsifiable concentrates using water. Dust-like and granulated preparations and sprayable solutions are no longer diluted with other inert substances before use.
  • the external conditions such as temperature, humidity, u. a. the required application rate varies. It is generally between 0.01 and 10 kg / ha, preferably about 0.1 to 5.0 kg / ha of active ingredient.
  • the new herbicides together with one or more herbicides, e.g. B. as a tank mix or in the form of a finished formulation to achieve further advantageous effects.
  • the active compounds according to the invention can be combined with other herbicides, insecticides and fungicides.
  • Concentrations between 0.01 and 1.25 kg / ha are suitable for use as growth regular notes.
  • Aqueous dispersions of wettable powders or dilutions of emulsifiable concentrates are preferably used. The application takes place in the post-emergence.
  • Preferred crops are corn and tobacco.
  • the reaction mixture is allowed to come to 0 ° C. in the course of one hour, cooled to -70 ° C., 9.35 g (0.1 mol) of O, N-dimethylhydroxylamine hydrochloride are added and 20.2 are added in the course of a further hour g (0.2 mol) of triethylamine- dissolved in 100 ml of dichloromethane. After stirring for 2 hours at ⁇ 70 ° C, stirring is continued for 18 hours at room temperature, washed with 0.5 N sodium acetate solution, then with saturated sodium chloride solution and the dichloromethane phase is dried over sodium sulfate.
  • the present compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial root weeds that are difficult to control are also well captured by the active ingredients. It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence spraying.
  • the compounds according to the invention are applied to the earth's surface in a pre-sowing or pre-emergence process before the weed plants germinate, the emergence of the seedlings is not prevented.
  • the weeds grow to the cotyledon stage, but then stop growing and eventually die completely after 3-5 weeks.
  • the active ingredients are applied to the green parts of the plant in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the crop plants harmful weed competition can be eliminated very early and sustainably by using the new agents according to the invention.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledon weeds, crop plants of economically important crops such as, for. B. wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged. Compared to the prior art, the substances according to the invention therefore have a significantly improved selectivity in crop plants.
  • the present compounds are very suitable for controlling undesirable plant growth in agricultural crops.
  • Seeds or rhizome pieces of mono- and dicotyledon weeds were placed in clay soil in plastic pots (0 9 cm) and covered with soil.
  • the compounds according to the invention formulated as wettable powders or as emulsion concentrates were applied to the surface of the earth in the form of aqueous suspensions or emulsions.
  • the amount of water applied per pot corresponded to the equivalent of 600-800 1 / ha.
  • the test pots were placed in the greenhouse and the test plants were cultivated under good growth conditions (temperature: 23 ⁇ 1 ° C; relative humidity 60-80%). After about 3 weeks, the plant damage was assessed visually. Untreated controls served as a comparison. Table 3 summarizes the pre-opening results.
  • test results shown demonstrate the excellent herbicidal pre-emergence effect of the new compounds according to the invention against grasses and weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (7)

1. Composés répondant à la formule 1 :
Figure imgb0041
dans laquelle
X représente ―O― ou ―SO2―,
Y représente CH ou l'azote,
R1 représente un alkyle en C1-C6, un alcényle eh C2-C6 ou un alcynyle en C2-C6, radicaux qui peuvent éventuellement porter un halogène, un alcoxy en C1-C4 ou un (C1-C4) alcoxy-carbonyle,
R2 représente l'hydrogène, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cyclohexyle,
R3 et R4 représentent chacun, indépendamment l'un de l'autre, l'hydrogène ou un alkyle en C1-C4,
R5 et R6 représentent chacun, indépendamment l'un de l'autre, l'hydrogène, un alkyle en C1-C4 ou un alcoxy en C1-C4 [ces radicaux pouvant éventuellement porter un ou plusieurs substituants pris parmi les halogènes, les alcoxy en C1-C4 et les alkylthio en C1-C4], un halogène, un alkylthio en C1-C4, un alkylamino en C1-C4 ou un di-(Ci-C4) alkyl-amino, et également, dans le cas où R2 ou R3 représente l'hydrogène, les sels physiologiquement acceptables qu'ils forment avec des bases.
2. Composés de formule 1 selon la revendication 1 dans lesquels : R1 et R2 représentent chacun, indépendamment l'un de l'autre, un alkyle en C1-C3 ou un alcényle contenant au plus 3 atomes de carbone, R3 et R4 représentent chacun l'hydrogène, R5 et R6 représentent chacun, indépendamment l'un de l'autre, un alkyle en C1 ou C2 ou un alcoxy en C1 ou C2, X représente ―SO2― et Y représente CH.
3. Procédé pour préparer des composés de formule I, procédé caractérisé en ce que :
a) on fait réagir des composés répondant à la formule III :
Figure imgb0042
dans laquelle R1, R2 et X ont les significations indiquées ci-dessus, avec des composés répondant à la formule IV :
Figure imgb0043
dans laquelle Z représente un atome de fluor ou de chlore ou un radical (C1-C4) alcoxy ou phénoxy éventuellement halogéné, mais représente plus particulièrement le chlore, et R4, R5, R6 et Y correspondent aux définitions qui ont été données pour les composés de formule I, ou
b) on fait réagir des composés répondant à la formule Il :
Figure imgb0044
dans laquelle Y, R5 et R6 correspondent aux définitions qui ont été données pour les composés de formule I, avec des composés répondant à la formule III représentée plus haut, ou
c) dans le cas où X représente un radical ―SO2― on fait réagir des composés répondant à la formule V :
Figure imgb0045
dans laquelle R1 et R2 correspondent aux définitions qui ont été données pour les composés de formule I, avec des composés répondant à la formule VI :
Figure imgb0046
dans laquelle R4, R5, R6 et Y ont les significations qui leur ont été précédemment données, et éventuellement on alkyle à la position de R2 ou de R3 les composés de formule I obtenus, dans lesquels R2 et R3 représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène.
4. Produits herbicides et régulateurs de croissance caractérisés en ce qu'ils contiennent des composés de formule I.
5. Application de composés de formule I à la lutte contre la végétation indésirable et à la régulation de la croissance.
6. Procédé pour combattre la végétation indésirable ou pour régler la croissance, procédé caractérisé en ce qu'on applique sur les plantes à traiter ou sur les surfaces cultivées une quantité efficace d'un composé de formule I.
7. Composés de formule Il selon la revendication 3.
EP84107833A 1983-07-09 1984-07-05 Urées N-alkoxy- et N-alkylsulfonylaminosulfonyliques et pyrimido- ou triazino-thiatriazine-oxides comme intermédiaires Expired EP0131258B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT84107833T ATE45948T1 (de) 1983-07-09 1984-07-05 Neue n-alkoxy- nalkylsulfonylaminosulfonylharnstoffe, und neue (pyrimido) triazino-thiatriazinoxide als vorprodukte.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3324802 1983-07-09
DE19833324802 DE3324802A1 (de) 1983-07-09 1983-07-09 Neue n-alkoxy- und n- alkylsulfonylaminosulfonylharnstoffe, und neue (pyrimido) triazino-thiadiazinoxide als vorprodukte

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EP0131258A2 EP0131258A2 (fr) 1985-01-16
EP0131258A3 EP0131258A3 (en) 1986-08-27
EP0131258B1 true EP0131258B1 (fr) 1989-08-30

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US (2) US4601747A (fr)
EP (1) EP0131258B1 (fr)
JP (1) JPH072724B2 (fr)
AR (1) AR244769A1 (fr)
AT (1) ATE45948T1 (fr)
AU (1) AU564963B2 (fr)
BR (1) BR8403383A (fr)
CA (1) CA1225640A (fr)
CS (1) CS416591A3 (fr)
DD (1) DD229015A5 (fr)
DE (2) DE3324802A1 (fr)
DK (1) DK166148C (fr)
ES (1) ES8503675A1 (fr)
HU (1) HU195613B (fr)
IL (1) IL72342A (fr)
NL (1) NL981003I2 (fr)
NZ (1) NZ208803A (fr)
PH (1) PH21737A (fr)
SU (1) SU1466634A3 (fr)
ZA (1) ZA845217B (fr)

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US10544426B2 (en) 2010-10-15 2020-01-28 Bayer Intellectual Property Gmbh Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants

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US11371057B2 (en) 2010-10-15 2022-06-28 Bayer Intellectual Property Gmbh Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants

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BR8403383A (pt) 1985-06-18
US4601747A (en) 1986-07-22
SU1466634A3 (ru) 1989-03-15
IL72342A (en) 1988-05-31
DE3479581D1 (en) 1989-10-05
EP0131258A2 (fr) 1985-01-16
PH21737A (en) 1988-02-10
NL981003I2 (nl) 1999-02-01
AU564963B2 (en) 1987-09-03
DE3324802A1 (de) 1985-01-17
NL981003I1 (nl) 1998-09-01
DD229015A5 (de) 1985-10-30
DK335284A (da) 1985-01-10
HU195613B (en) 1988-06-28
ATE45948T1 (de) 1989-09-15
DK335284D0 (da) 1984-07-06
DK166148B (da) 1993-03-15
EP0131258A3 (en) 1986-08-27
ZA845217B (en) 1985-02-27
HUT36997A (en) 1985-11-28
CS416591A3 (en) 1992-05-13
ES534114A0 (es) 1985-04-01
NZ208803A (en) 1987-10-30
JPS6048973A (ja) 1985-03-16
AU3043284A (en) 1985-01-10
CA1225640A (fr) 1987-08-18
JPH072724B2 (ja) 1995-01-18
US4718937A (en) 1988-01-12
AR244769A1 (es) 1993-11-30
ES8503675A1 (es) 1985-04-01
DK166148C (da) 1993-08-09
IL72342A0 (en) 1984-11-30

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